TWI666215B - 有機電場發光元件用材料及使用其的有機電場發光元件 - Google Patents
有機電場發光元件用材料及使用其的有機電場發光元件 Download PDFInfo
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- TWI666215B TWI666215B TW104109271A TW104109271A TWI666215B TW I666215 B TWI666215 B TW I666215B TW 104109271 A TW104109271 A TW 104109271A TW 104109271 A TW104109271 A TW 104109271A TW I666215 B TWI666215 B TW I666215B
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- aromatic
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- 239000000463 material Substances 0.000 title claims abstract description 104
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- 125000003118 aryl group Chemical group 0.000 claims description 79
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 59
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- 238000005215 recombination Methods 0.000 description 4
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- KLCLIOISYBHYDZ-UHFFFAOYSA-N 1,4,4-triphenylbuta-1,3-dienylbenzene Chemical class C=1C=CC=CC=1C(C=1C=CC=CC=1)=CC=C(C=1C=CC=CC=1)C1=CC=CC=C1 KLCLIOISYBHYDZ-UHFFFAOYSA-N 0.000 description 3
- JTWMOWRMSZZHDR-UHFFFAOYSA-N 7-(5-hydroxy-2-methylphenyl)-6-(2-methoxyphenyl)-4-methylpurino[7,8-a]imidazole-1,3-dione Chemical compound COC1=CC=CC=C1N(C(=CN12)C=3C(=CC=C(O)C=3)C)C2=NC2=C1C(=O)NC(=O)N2C JTWMOWRMSZZHDR-UHFFFAOYSA-N 0.000 description 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 3
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- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 3
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- QKTRRACPJVYJNU-UHFFFAOYSA-N thiadiazolo[5,4-b]pyridine Chemical class C1=CN=C2SN=NC2=C1 QKTRRACPJVYJNU-UHFFFAOYSA-N 0.000 description 3
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- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 2
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- ZHFLRRPGAVPNMB-UHFFFAOYSA-N 1-[3-(9h-carbazol-1-yl)phenyl]-9h-carbazole Chemical compound C12=CC=CC=C2NC2=C1C=CC=C2C1=CC(C2=C3NC=4C(C3=CC=C2)=CC=CC=4)=CC=C1 ZHFLRRPGAVPNMB-UHFFFAOYSA-N 0.000 description 1
- FBTOLQFRGURPJH-UHFFFAOYSA-N 1-phenyl-9h-carbazole Chemical compound C1=CC=CC=C1C1=CC=CC2=C1NC1=CC=CC=C12 FBTOLQFRGURPJH-UHFFFAOYSA-N 0.000 description 1
- BRSRUYVJULRMRQ-UHFFFAOYSA-N 1-phenylanthracene Chemical compound C1=CC=CC=C1C1=CC=CC2=CC3=CC=CC=C3C=C12 BRSRUYVJULRMRQ-UHFFFAOYSA-N 0.000 description 1
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
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- RDRCCJPEJDWSRJ-UHFFFAOYSA-N pyridine;1h-pyrrole Chemical class C=1C=CNC=1.C1=CC=NC=C1 RDRCCJPEJDWSRJ-UHFFFAOYSA-N 0.000 description 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical class C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- CEWNHRJKXUISET-UHFFFAOYSA-N quinolin-8-ol;1h-quinolin-2-one Chemical class C1=CN=C2C(O)=CC=CC2=C1.C1=CC=C2NC(=O)C=CC2=C1 CEWNHRJKXUISET-UHFFFAOYSA-N 0.000 description 1
- QEVBPWGFJKJQHA-UHFFFAOYSA-N quinolino[6,5-f]quinoline Chemical compound C1=CC=NC2=CC=C(C=3C(=NC=CC=3)C=C3)C3=C21 QEVBPWGFJKJQHA-UHFFFAOYSA-N 0.000 description 1
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- 230000009467 reduction Effects 0.000 description 1
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- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- NZFNXWQNBYZDAQ-UHFFFAOYSA-N thioridazine hydrochloride Chemical class Cl.C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C NZFNXWQNBYZDAQ-UHFFFAOYSA-N 0.000 description 1
- 238000001269 time-of-flight mass spectrometry Methods 0.000 description 1
- OVTCUIZCVUGJHS-VQHVLOKHSA-N trans-dipyrrin Chemical compound C=1C=CNC=1/C=C1\C=CC=N1 OVTCUIZCVUGJHS-VQHVLOKHSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
- C09K11/025—Use of particular materials as binders, particle coatings or suspension media therefor non-luminescent particle coatings or suspension media
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- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
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| JP2014-059925 | 2014-03-24 | ||
| JP2014059925 | 2014-03-24 |
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| TW201536796A TW201536796A (zh) | 2015-10-01 |
| TWI666215B true TWI666215B (zh) | 2019-07-21 |
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| EP (1) | EP3125326B1 (ko) |
| JP (1) | JP6402176B2 (ko) |
| KR (1) | KR102241664B1 (ko) |
| CN (1) | CN106165139B (ko) |
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| US10529932B2 (en) * | 2014-03-24 | 2020-01-07 | Nippon Steel Chemical & Material Co., Ltd. | Organic-electroluminescent-element material and organic electroluminescent element using same |
| US10446767B2 (en) | 2014-03-28 | 2019-10-15 | Nippon Steel Chemical & Material Co., Ltd. | Organic-electroluminescent-element material and organic electroluminescent element using same |
| JP6307332B2 (ja) * | 2014-04-21 | 2018-04-04 | 新日鉄住金化学株式会社 | 有機電界発光素子 |
| US10807996B2 (en) | 2015-03-30 | 2020-10-20 | Nippon Steel Chemical & Material Co., Ltd. | Material for organic electroluminescent element and organic electroluminescent element in which same is used |
| US20190103563A1 (en) * | 2016-03-28 | 2019-04-04 | Nippon Steel & Sumikin Chemical Co., Ltd. | Organic electroluminescent element |
| US10978647B2 (en) | 2017-02-15 | 2021-04-13 | Universal Display Corporation | Organic electroluminescent materials and devices |
| CN107353302A (zh) * | 2017-07-03 | 2017-11-17 | 南京邮电大学 | 一种基于咔唑的碳硼烷衍生物材料及其制备方法与应用 |
| KR20200132898A (ko) * | 2018-03-19 | 2020-11-25 | 닛테츠 케미컬 앤드 머티리얼 가부시키가이샤 | 유기 전계발광 소자 |
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| JP2005166574A (ja) * | 2003-12-05 | 2005-06-23 | Canon Inc | 有機発光素子 |
| US20110278556A1 (en) * | 2010-05-14 | 2011-11-17 | Universal Display Corporation | Azaborinine Compounds As Host Materials And Dopants For PHOLEDs |
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| ATE511222T1 (de) | 1999-12-01 | 2011-06-15 | Univ Princeton | Komplex der formel l2irx |
| JP2001313178A (ja) | 2000-04-28 | 2001-11-09 | Pioneer Electronic Corp | 有機エレクトロルミネッセンス素子 |
| JP4387781B2 (ja) * | 2003-12-05 | 2009-12-24 | キヤノン株式会社 | カルボラン化合物及び導電材料 |
| US7547501B2 (en) | 2006-10-05 | 2009-06-16 | Az Electronic Materials Usa Corp. | Photoactive compounds |
| DE102007031261A1 (de) | 2007-07-05 | 2009-01-08 | Universtität Regensburg | Lumineszierende Metallkomplexe mit sperrigen Hilfsliganden |
| WO2009085344A2 (en) | 2007-12-28 | 2009-07-09 | Universal Display Corporation | Dibenzothiophene-containing materials in phosphorescent light emitting diodes |
| JP2010059128A (ja) * | 2008-09-05 | 2010-03-18 | Nagoya Univ | ２炭素置換カルボラン型溶融塩及びその製造方法 |
| TWI477579B (zh) * | 2010-02-12 | 2015-03-21 | Nippon Steel & Sumikin Chem Co | Organic electroluminescent elements |
| WO2013088934A1 (ja) * | 2011-12-12 | 2013-06-20 | 新日鉄住金化学株式会社 | 有機電界発光素子用材料及びそれを用いた有機電界発光素子 |
| JP5760282B2 (ja) * | 2011-12-19 | 2015-08-05 | ヨル チョン ケミカル カンパニーリミテッドＹｏｕｌ Ｃｈｏｎ Ｃｈｅｍｉｃａｌ Ｃｏ．， Ｌｔｄ． | 安定性を有する新規化合物、これを含む電荷輸送材料および青色リン光有機ｅｌ素子 |
| US10529932B2 (en) * | 2014-03-24 | 2020-01-07 | Nippon Steel Chemical & Material Co., Ltd. | Organic-electroluminescent-element material and organic electroluminescent element using same |
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- 2015-02-23 KR KR1020167029298A patent/KR102241664B1/ko active IP Right Grant
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- 2015-02-23 EP EP15770335.6A patent/EP3125326B1/en not_active Not-in-force
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005166574A (ja) * | 2003-12-05 | 2005-06-23 | Canon Inc | 有機発光素子 |
| US20110278556A1 (en) * | 2010-05-14 | 2011-11-17 | Universal Display Corporation | Azaborinine Compounds As Host Materials And Dopants For PHOLEDs |
Also Published As
| Publication number | Publication date |
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| KR20160137587A (ko) | 2016-11-30 |
| CN106165139A (zh) | 2016-11-23 |
| JPWO2015146417A1 (ja) | 2017-04-13 |
| EP3125326A4 (en) | 2017-11-08 |
| TW201536796A (zh) | 2015-10-01 |
| WO2015146417A1 (ja) | 2015-10-01 |
| EP3125326A1 (en) | 2017-02-01 |
| US20160380199A1 (en) | 2016-12-29 |
| US10305048B2 (en) | 2019-05-28 |
| KR102241664B1 (ko) | 2021-04-19 |
| EP3125326B1 (en) | 2018-08-29 |
| JP6402176B2 (ja) | 2018-10-10 |
| CN106165139B (zh) | 2018-04-20 |
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